Find Cheap Flights from Caribbean to Chicago

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Caribbean to Chicago

(Round-trip)
Depart: Mon Aug 28 2017 Return: Tue Sep 5 2017 Trip spans 9 days
Frontier
Frontier
SJU
ORD
17h 37m
1 stop
ORD
SJU
17h 40m
1 stop
Depart: Sun Sep 10 2017 Return: Mon Sep 11 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 50m
1 stop
ORD
BQN
7h 36m
1 stop
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
JetBlue
JetBlue
NAS
ORD
8h 54m
1 stop
ORD
NAS
9h 48m
1 stop
Depart: Wed Dec 20 2017 Return: Wed Jan 3 2018 Trip spans 15 days
United
United
MBJ
ORD
4h 25m
nonstop
ORD
MBJ
7h 10m
1 stop
Depart: Thu Oct 19 2017 Return: Tue Oct 24 2017 Trip spans 6 days
Delta
Delta
STT
MDW
9h 37m
1 stop
MDW
STT
6h 27m
1 stop
Depart: Fri Aug 25 2017 Return: Sun Aug 27 2017 Trip spans 3 days
American Airlines
American Airlines
GCM
ORD
18h 41m
2 stops
ORD
GCM
8h 04m
1 stop
Depart: Fri Nov 17 2017 Return: Fri Dec 1 2017 Trip spans 15 days
Copa Airlines
Copa Airlines
STI
ORD
9h 18m
1 stop
ORD
STI
23h 36m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 26 2017 Trip spans 16 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
9h 10m
1 stop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 43m
1 stop
ORD
SJU
8h 25m
1 stop
Depart: Wed Oct 18 2017 Return: Tue Oct 24 2017 Trip spans 7 days
Delta
Delta
SJU
MDW
10h 37m
2 stops
MDW
SJU
13h 53m
2 stops
Depart: Wed Sep 13 2017 Return: Sun Sep 24 2017 Trip spans 12 days
United
United
SJU
ORD
5h 05m
nonstop
ORD
SJU
4h 40m
nonstop
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
JetBlue
JetBlue
NAS
ORD
6h 17m
1 stop
ORD
NAS
5h 56m
1 stop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
6h 54m
1 stop
Depart: Thu Aug 10 2017 Return: Mon Aug 14 2017 Trip spans 5 days
Frontier
Frontier
SJU
ORD
17h 27m
1 stop
ORD
SJU
17h 40m
1 stop
Depart: Sat Dec 23 2017 Return: Sat Jan 6 2018 Trip spans 15 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 35m
nonstop
Depart: Thu Oct 5 2017 Return: Tue Oct 10 2017 Trip spans 6 days
Delta
Delta
SJU
MDW
9h 53m
1 stop
MDW
SJU
13h 53m
2 stops
Depart: Thu Aug 31 2017 Return: Sun Sep 3 2017 Trip spans 4 days
American Airlines
American Airlines
SJU
ORD
5h 17m
nonstop
ORD
SJU
4h 42m
nonstop
Depart: Tue Nov 7 2017 Return: Sun Nov 12 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 42m
1 stop
ORD
SJU
6h 55m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Aguadilla
$311
Nassau
$322
San Juan
$279
Saint Thomas Island
$348
Montego Bay
$343
George Town
$405
Santiago de los Caballeros
$509
Destination

Chicago
only $279
only $348
Airlines Airline reviews

2 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 5.7.

Overall
6.0
Boarding
4.0
Crew
6.0
Comfort
6.0
Food
6.0
Entertainment
6.0